title: Biosynthesis and enantioselectivity in the production of the lilac compounds in Actinidia arguta flowers.
abstract: Biosynthesis of the lilac alcohols and alcohol epoxides from linalool in 'Hortgem Tahi' kiwifruit (Actinidiaarguta) flowers was investigated by incubating flowers with rac-linalool, rac-[4,4,10,10,10-(2)H(5)]linalool, (R)-8-hydroxylinalool and (R)-8-oxolinalool. All substrates were incorporated into the lilac alcohols although the (R)-configured compounds are not normally present in flowers. Biosynthesis of the lilac alcohol epoxides from rac-1,2-epoxy[4,4,10,10,10-(2)H(5)]linalool and rac-[4',4', 8', 8',8'-(2)H(5)]lilac aldehyde epoxide, rather than the lilac alcohols, was examined. Both substrates were non-enantioselectively converted to the lilac alcohol epoxides, suggesting two biosynthetic pathways for these compounds, contrary to previous reports. Their ability to process unnatural substrates indicates that A.arguta flowers have a greater biosynthetic capability than is suggested by their phytochemical composition. Linalool, the lilac compounds, and their biosynthetic intermediates were measured in the pistils, stamen, petals and sepals to determine if localisation in different organs contributed to only (S)-linalool being processed to the lilac compounds. Both linalool enantiomers were present in all organs, while most (97%) of the lilac compounds, and their precursors, were found in the petals. (S)-Linalool was not depleted from the flower petals, with respect to (R)-linalool, during the time of maximum production of the metabolites of (S)-linalool.
authors.affiliation: The New Zealand Institute for Plant & Food Research Limited (Plant & Food Research), Private Bag 11600, Palmerston North 4442, New Zealand. adam.matich@plantandfood.co.nz
authors.forename: A J
authors.initials: AJ
authors.lastname: Matich
authors.forename: D J
authors.initials: DJ
authors.lastname: Comeskey
authors.forename: B J
authors.initials: BJ
authors.lastname: Bunn
authors.forename: M B
authors.initials: MB
authors.lastname: Hunt
authors.forename: D D
authors.initials: DD
authors.lastname: Rowan
mesh_terms: D029042:Actinidia / Q000254:growth & development / Q000378:metabolism*; D000080462:Acyclic Monoterpenes; D000447:Aldehydes / Q000737:chemistry / Q000378:metabolism; D005027:Ethylene Oxide / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D035264:Flowers / Q000254:growth & development / Q000378:metabolism; D005663:Furans / Q000737:chemistry* / Q000378:metabolism*; D039821:Monoterpenes / Q000737:chemistry / Q000378:metabolism; D020005:Propanols / Q000737:chemistry* / Q000378:metabolism*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: C512448:2-(5-methyl-5-(oxiran-2-yl)-tetrahydrofuran-2-yl)propan-1-ol; D000080462:Acyclic Monoterpenes; D000447:Aldehydes; D005663:Furans; D039821:Monoterpenes; D020005:Propanols; C018584:linalool; D005027:Ethylene Oxide